Highly efficient and enantioselective cyclization of aromatic imines via directed C-H bond activation

Article abstract of DOI:10.1021/ja0394986

The first highly enantioselective catalytic reaction involving aromatic C-H bond activation is communicated. Enantioselective cyclization of aromatic ketimines containing alkenyl groups tethered at the meta position of an imine directing group has been achieved using 5 mol % [RhCl(coe)₂]₂ and 15 mol % of an (S)-binol-derived phosphoramidite ligand. Selectivities of up to 96% ee and up to quantitative yields were obtained. Moreover, the identified catalyst system enables the intramolecular alkylation reaction to be performed at temperatures 75 °C lower than our previously reported achiral system. The reaction can even be performed at room temperature for one of the optimal substrates. Copyright